Artie Wins $10,000 at Baseball—Then Loses It on One Spin | Howard Stern Show 2026

Artie Lange wins $10,000 in a baseball challenge against pitcher Ila Borders—then loses the entire prize on a single roulette spin. Howard Stern follows every twist during this Las Vegas broadcast from the Hard Rock Hotel and Casino. After a rough night and plenty of doubts about his condition, Artie steps up to the plate. Michael Buffer delivers the introductions, Howard calls the action, and Artie waits for a pitch he can hit. His successful hit earns him the $10,000 prize—but the challenge includes taking those winnings to the roulette table. A last-minute disagreement over whether Artie must bet red delays the action. Once the confusion is cleared up, he chooses black in honor of Yankees player Mickey Rivers. The wheel lands on green, ending Artie’s chance to double the prize. The compilation then shifts to baseball talk, Artie’s memories of heckling at games, and Gary Dell’Abate’s account of an extraordinary Rock & Roll Hall of Fame concert. Gary also explains how dinner with Ross turned into a $485 sushi bill before tip, prompting Howard and the staff to question what could possibly justify the price. The closing section features commentary on a televised Chaz Bono interview. CHAPTERS 00:00:00 Artie apologizes for the previous night 00:02:09 Meeting pitcher Ila Borders 00:03:03 Ila’s baseball background and Artie’s confidence 00:06:38 Michael Buffer introduces the baseball challenge 00:10:34 The first pitches and the $10,000 prize 00:12:12 Walks do not count: the challenge continues 00:15:09 Artie gets the hit and wins $10,000 00:16:38 The winnings must go to roulette 00:19:00 Back inside the Hard Rock Hotel and Casino 00:22:14 Artie prepares to bet the entire prize 00:23:37 Does Artie have to choose red? 00:25:48 Tom clears up the betting-rule confusion 00:26:33 Artie chooses black in honor of Mickey Rivers 00:28:01 One spin decides the $10,000 00:28:44 Yankees, A-Rod, and the World Series 00:33:00 Expensive stadium food and frustrated fans 00:36:00 Artie recalls heckling at baseball games 00:41:23 Gary’s Rock & Roll Hall of Fame concert recap 00:46:55 Dinner with Ross and an unexpected sushi bill 00:48:14 Gary reveals the $485 total before tip 00:51:43 The staff questions the sushi-bar experience 00:53:15 Commentary on a Chaz Bono interview KEYWORDS Howard Stern, Howard Stern Show, classic Howard Stern, Stern Show archive, Artie Lange, Artie Lange baseball challenge, Artie Lange Ila Borders, Ila Borders pitcher, Artie wins 10000 dollars, Artie Lange roulette, Artie loses 10000 dollars, Artie bets on black, Howard Stern Las Vegas, Hard Rock Hotel casino broadcast, Michael Buffer Artie Lange, Gary Dell’Abate, Gary expensive sushi dinner, Gary 485 dollar sushi bill, Rock and Roll Hall of Fame concert, Artie Lange Yankees stories #howardstern #artielange #IlaBorders #GaryDellAbate #ClassicHowardStern #sternshow